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The Elder Scrolls V: Skyrim Game Add-Ons (DLC) Hints
Where can I find dragons on Solstheim?
1 of 4: Note that killing dragons on Solstheim has the disadvantage of there being a chance that Miraak will show up and steal a dragon's soul from you after you kill it.
2 of 4: There'll be a dragon at Saering's Watch, unless you killed it recently.
3 of 4: There may also be one on the second island that's NW of Frossel, due to the presence of a dragon mound there.
4 of 4: You can try fast-traveling back and forth between Raven Rock and Tel Mithryn to see if any dragons will randomly appear and attack either one of those places. (They frequently did when I played with my level 81 character, but never did when I played with a low-level character.)